Find Hotels with a Pool in Wainscott, NY

  • Upfront pricing

    Our total price for your stay includes taxes and fees
  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
  • Be picky

    Search almost a million properties worldwide

Check availability on Wainscott Hotels with a Pool

Next weekend
In two weeks

Our top choices for Wainscott hotels with a pool

The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (242 reviews)
  • cleanliness
    Take a summer dip in the seasonal outdoor pool with loungers for relaxing in the Hamptons sun.
$264 nightly
The price is $297
May 4 - May 5
Total with taxes and fees
The Sagaponack

Wainscott Woods Retreat

Wainscott Woods Retreat
2.5 star property
Wainscott
7.0 out of 10, Good, (9 reviews)
  • cleanliness
    Seasonal outdoor pool at oceanfront hotel offers garden views and nearby vineyard tours for summer retreats.
$585 nightly
The price is $668
Apr 25 - Apr 26
Total with taxes and fees
Wainscott Woods Retreat

Ocean Resort Inn

Ocean Resort Inn
2.0 star property
Downtown Montauk
9.6 out of 10, Exceptional, (487 reviews)
  • cleanliness
    Soak in coastal charm at the heated saltwater pool steps from Montauk's sandy shores.
$125 nightly
The price is $143
May 3 - May 4
Total with taxes and fees
Ocean Resort Inn

Montauk Blue Hotel

Montauk Blue Hotel
2.0 star property
Downtown Montauk
9.2 out of 10, Wonderful, (188 reviews)
  • cleanliness
    Dive into seaside bliss with Montauk Blue Hotel's indoor pool and hot tub, just steps from sandy shores.
$145 nightly
The price is $165
Apr 27 - Apr 28
Total with taxes and fees
Montauk Blue Hotel

Ocean Surf Resort

Ocean Surf Resort
2.0 star property
Downtown Montauk
8.4 out of 10, Very Good, (235 reviews)
  • cleanliness
    Seasonal Montauk retreat with sun-drenched pool deck offering ocean views, just steps from downtown.
$93 nightly
The price is $106
Apr 30 - May 1
Total with taxes and fees
Ocean Surf Resort

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
$167 nightly
The price is $191
Apr 21 - Apr 22
Total with taxes and fees
North Fork Cottages & RV Resort

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (127 reviews)
$258 nightly
The price is $295
Apr 27 - Apr 28
Total with taxes and fees
Offshore Montauk

The Penny Lane

The Penny Lane
2.0 star property
Hampton Bays
9.0 out of 10, Wonderful, (77 reviews)
  • cleanliness
    Seasonal poolside relaxation awaits at this oceanfront hotel with sun loungers, umbrellas, and gardens.
$200 nightly
The price is $229
May 7 - May 8
Total with taxes and fees
The Penny Lane

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,325 reviews)
  • cleanliness
    Refreshing hilltop retreat with year-round pool access and sweeping ocean vistas.
$168 nightly
The price is $192
Apr 21 - Apr 22
Total with taxes and fees
Montauk Manor

Marram

Marram
4.0 star property
Montauk
8.8 out of 10, Excellent, (253 reviews)
  • cleanliness
    Cool ocean-adjacent pool getaway with loungers, umbrellas, and beach perks for the perfect summer splash.
$337 nightly
The price is $385
Apr 21 - Apr 22
Total with taxes and fees
Marram
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Choose what matters most at hotels with a pool in Wainscott

Top Wainscott Hotel Reviews

Frequently asked questions

How much does a hotel with outdoor pool in Wainscott cost?
Enjoy staying in a hotel in Wainscott with an outdoor pool. You can find a great deal from $106 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Are there hotels in Wainscott with outdoor pool cabanas or loungers?
The Sagaponack is a charming 3-star hotel in Wainscott that offers a delightful outdoor pool experience. Guests rave about the inviting pool area, featuring comfortable sun loungers and shaded umbrellas, great for lounging on a sunny day. With a review rating of 8.8, visitors appreciate the hotel's friendly staff and the nice decor that adds to the overall appeal.

Beyond the pool, The Sagaponack also provides complimentary toiletries and free WiFi, ensuring a convenient stay for families. Plus, self-parking is available at no additional cost, making it easy to explore the beautiful surroundings of Wainscott.
Is it cheaper to book flights and a Wainscott hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
How can I save on a Wainscott hotel with a pool with Expedia?
Before booking your Wainscott hotel, remember to join One Key™, Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Wainscott for you.

Explore a world of travel with Expedia